Book Exclusive Pittsfield Vacation Packages

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Pittsfield flight + hotel packages

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Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Save 100% on your flight
per person
Jun. 5 - Jun. 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this business-friendly hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this 4-star luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Lexington Battle Green and Burlington Mall are located nearby.
Riverview Resort

Riverview Resort

3 out of 5
Bass River
Save 100% on your flight
per person
Jun. 5 - Jun. 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this 3-star aparthotel in South Yarmouth. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.
Sea Mist Resort

Sea Mist Resort

3 out of 5
Save 100% on your flight
per person
Jun. 5 - Jun. 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this 3-star business-friendly aparthotel in Mashpee. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Mashpee Commons and Cape Cod Children's Museum are located nearby.
Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Boston (BOS)
Stay at this 4-star family-friendly aparthotel in Boston. Enjoy free WiFi, a fitness center, and parking (surcharge). Popular attractions Boston Harbor and New England Aquarium are located nearby.

Top Pittsfield hotels deals

Steele Hill Resorts

Steele Hill Resorts

3 out of 5
516 Steele Hill Road, Sanbornton, NH
The price is CA $265 per night
CA $265
CA $287 total
includes taxes & fees
2 Apr - 3 Apr
Stay at this 3-star spa hotel in Sanbornton. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Ahern State Park and Sanbornton Public Library are located nearby.
Pool
Hot tub
Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

2.5 out of 5
75 Tilton Road, NH Route 140, Tilton, NH
Free cancellation
The price is CA $169 per night
CA $169
CA $183 total
includes taxes & fees
9 Apr - 10 Apr
Book a stay at this business-friendly hotel in Tilton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanger Outlets Tilton and Tilton Center are located nearby.
Pool
Breakfast included
Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

2.5 out of 5
480 Main Street, Laconia, NH
Free cancellation
Reserve now, pay when you stay
The price is CA $139 per night
CA $139
CA $151 total
includes taxes & fees
3 Apr - 4 Apr
Book a stay at this business-friendly hotel in Laconia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bank of New Hampshire Pavilion at Meadowbrook and Gunstock Mountain Resort are located nearby.
Pool
Breakfast included
Fairfield Inn By Marriott Concord

Fairfield Inn By Marriott Concord

2.5 out of 5
4 Gulf St, Concord, NH
Free cancellation
Reserve now, pay when you stay
The price is CA $177 per night
CA $177
CA $193 total
includes taxes & fees
7 Apr - 8 Apr
Book a stay at this business-friendly hotel in Concord. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Capitol Center for the Arts and New Hampshire State House are located nearby.
Pool
Breakfast included
Fireside Inn & Suites Gilford

Fireside Inn & Suites Gilford

2.5 out of 5
17 Harris Shore Road, Gilford, NH
Free cancellation
Reserve now, pay when you stay
The price is CA $224 per night
CA $224
CA $243 total
includes taxes & fees
3 Apr - 4 Apr
Book a stay at this business-friendly hotel in Gilford. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Lake Winnipesaukee and Bank of New Hampshire Pavilion at Meadowbrook are located nearby.
Pool
Hot tub
Comfort Inn Concord

Comfort Inn Concord

2.5 out of 5
71 Hall St, Concord, NH
The price is CA $153 per night
CA $153
CA $166 total
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this business-friendly hotel in Concord. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Capitol Center for the Arts and Rotary Park are located nearby.
Pool
Hot tub
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Harold Conrad Square

After visiting Harold Conrad Square, make a plan to see the other sights and activities in Pittsfield.

Harold Conrad Square

Josiah Carpenter Library

Josiah Carpenter Library is just one of the places to see in Pittsfield, so why not enjoy the other things to explore during your travels?

Josiah Carpenter Library

Scenic Theatre

You can enjoy a show at Scenic Theatre on your trip to Pittsfield.

Scenic Theatre

Pittsfield Vacations

If you're vacationing in Pittsfield and you don't really know a great deal about it, don't worry — we can fill you in!

This town is located 9 miles (14 kilometers) northeast of Pembroke. You'll also find it 13 miles (21 kilometers) northeast of Concord.

2,000 friendly locals reside in this part of New Hampshire.

Places to visit in Pittsfield

Ever wondered what Saturn's rings are made of or just what a black hole is? Learn all about the stars, moons and the mysteries of the universe at Christa McAuliffe Planetarium. Want more ideas? Ever wondered how people lived without the mod cons we enjoy today? Amble down the old streets of Canterbury Shaker Village and experience life as it was lived many years ago.

Where do you fly into for Pittsfield?

While you're researching for your Pittsfield escape, bear in mind that the closest terminal, Manchester-Boston Regional Airport (MHT), is approximately 25 miles (40 kilometers) south of the main streets. Book your flights, fill up your suitcase and get ready for an once-in-a-lifetime adventure!

Frequently asked questions

How much are vacation packages to Pittsfield?
With Travelocity vacation packages, you could live it up in Pittsfield from just CA $930. Activities, flights and hotels — we’ve got you. You’ll save loads just for bundling together your bookings. And with everything taken care of before you go, you can sit back, relax and enjoy the adventure.
Where can I get the best vacation package deals for Pittsfield?
You can lock in awesome Pittsfield package deals with Travelocity. Select from as many as 400 air carriers and 1,000,000 worldwide properties and turn those travel fantasies into reality.
Why should I book my Pittsfield vacation package with Travelocity?
The three S’s — savings, support and a stress-free booking — are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you can rely on our expert team of customer support professionals 24/7. With the Travelocity Price Match Guarantee, you know you’ll always get the best deal available.
Will I save money on my Pittsfield car rental if I bundle it with a hotel or flight?
Combining your car, hotel and flight into a Pittsfield vacation package is a great way to land the best prices. Plus, having your own wheels gives you absolute freedom to make your way to all the landmarks you can’t wait to see. Situated 105 kilometers from Pittsfield, Fenway Park is one place that should be on your must-do list. Fill up the tank and make a day trip of it.
Which airport is best for Pittsfield?
Portland Intl. Jetport Airport (PWM) is one of the most popular airports in Pittsfield. It’s situated 88 kilometers northeast of the bustling downtown area. Your other choices are Manchester-Boston Regional Airport (MHT) (40 kilometers away from central Pittsfield) and Lebanon Municipal Airport (LEB) (88 kilometers away from central Pittsfield).
Where should I stay when visiting Pittsfield?
The Vasha is a cozy pet-friendly lake house for relaxing in a secluded location. is the first choice of many travelers. Book now to avoid missing out.

Photos of local treasures

Browse Pittsfield vacation photos for more inspiration